Process of alcoholysis



ROCESS OF ALCOHOLYSIS Filed April 5 1921 A TTOR/VEY I 30 reaction. Thealcohol may be removed in in the usual way with the aid of inlet andPatented Apr. 22, 1924, 1,491,076

UNITED STATES PATENTOIFFICE.

LLOYD M. BURGHART, OF BALTIMORE, MARYLAND, ASSIGNOR TO U. S. INDUSTRIALALCOHOL 00., A CORPORATION OF WEST VIRGINIA.

PROCEQS OF ALCOHOLYSIS.

Application filed April 5, 1921. Serial Ito. 458,847.

To all whom it may concern: valved draw-off pipe 3 at the bottomthereof. 65

Be it known that I, LLOYD M. BURGHART, If it should be desired tooperate the appaa citizen of the UnitedStates, residing at ratus withabatch processl provide a valved Baltimore, State of Maryland, have ininlet pipe 4 at the top of the still 1. Pref- 5 vented certain new anduseful Imp-roveerably, however, the process is operated conments inProcesses of Alcoholysis, of which tinuously, and the materials used inthe re- 0 the following is a specification. action in the continuousprocess are intro- My invention relates particularly to a duced atanother part of the apparatus as process of alcoholysis, that is, aprocess in hereinafter described. The vapors evolved which an ester istreated with an alcohol in from the still 1 pass out of the same by sucha manner as to displace the basic radimeans of a pipe 5 to a rectifyingcolumn 65 cal of the ester, thus obtaining a new ester 6 which has aliquid sealed return pipe 7 for in which the basic radical of the esterreturning'amyl acetate formed in the retreated is substituted by thecorresponding action to the still 1. The amyl acetate is radical of thealcohol. formed by introducing three to four parts The object: of myinvention is to rovide by Weight of commercial methyl acetate, 7 aprocess whereby esters may be obtained that is to say, containing by wayof example, from other esters by substituting the basic ,85% of methylacetate and 15% of methyl radical therein with the correspondingradialcohol, into the column through an inlet cal contained in analcohol, the same being 1pipe 8 near the bottom thereof, and one partconducted so as to carry the reaction bey weight of amyl alcohol mixedwith a 7 yond the equilibrium point, thereby obtainquantity of strongsulfuric acid having a ing increased yields of the ester formed anddensity of 66 B. amounting to from .3 to thus enabling the products tobe produced 5% by weight of the other materials present,

on a commercial scale. In order to accomthrough an inlet pipe 9locatedat the top of plish this I provide a process in which one the column 6.The vapors from the column .or' more of the end products formed may passout by a pipe 10 to a dephlegmator 11 be removed, preferablycontinuously, such, having a liquid sealed return pipe 12 leading forexample, as the alcohol obtained in the to the column. The de'phlegmator11 is cooled any desired way as, for example, in the outlet pipes 13 and14. Vapors from the form of a constant boiling mixture withandephlegmator pass through a pipe 15 to a other one of the othermaterials present. In condenser 16 cooled by a current of water, orderto accomplish this I prefer to use a passing through inlet and outletpipes 17 35 higher alcohol than the alcohol formed in and 18. -Thecondensate passes out through the reaction to enable the latter to bemore a pipe 19.

.readily removed.' In the operation of my process, assuming Furtherobjects of m invention will the same to be continuous, the mixture ofappear from the detailed escription thereof sulfuric acid and amylalcohol is introduced 10 contained hereinafter. at th top of the column6 while the methyl While my invention is capable of being acetate isintroduced near the bottom thereas carried out in various ways, toillustrate of. Heat is applied to the materials which the invention, Ishall describe only certain reach the still 1, so as to maintain thestill ways of conducting the same hereinafter, at a boiling temperature.Amyl acetate is $5 and while it is capable of being carried out formedin the still 1 and in the column 6 with various types of apparatus Ihave and the vapors pass up through thepipe 5, shown only one type ofapparatus for use into the column 6 and then through the therewith inthe accompanying drawings, dephlegmator 11 to the condenser 16, where inwhich the condensed constant boiling mixture con- 50 The figure is adiagrammatic representataining 18% methyl alcohol and 82% methyl tion ofan apparatus which may be used in acetate is recovered. The methylalcohol carrying out my invention. formed in the reaction is thus beingcontinu- In the drawings I have shown a pot still ally removed and thereaction is therefore 1 heated by a steam coil 2 and having a conductedbeyond the equilibrium stage. In

this way large yields of the amylacetate are obtainable and the processrendered available for commercial use. In conducting the process anendeavor is made to remove as much of the alcohol as possible so as tocarry the process as far as the nature of the mate rials used willpermit. The removal during the reaction of the one or more of the endproducts formed in the reaction may be accomplished in'any desired Way,as, for example, by distillation, salting out, extraction, washing,precipitation with the addition of a third material, or by decompositionthereof. In the particular process described in detail above, however,the process is so arranged as to form an alcohol that boils at a lowerpoint than the alcohol added to the reaction mixture so as to enable itto be readily removed by distillation.

Other esters than amyl acetate may be produced by the use of differentreacting materials, such, for example, as methyl formats and amylalcohol, methyl acetate and butyl alcohol. Also, other catalysts may beused instead of sulfuric acid, such as other mineral acids, for example,hydrochloric acid, also sodium alcoholate, sodium hydroxide or bariumhydroxide, and where anhydrous esters are used metallic sodium may bethe catalyst utilized.

While I have described my invention above in detail it is to beunderstood that various changes are possible therein without departingfrom the spirit of the invention.

I claim:

1. The process which comprises reacting upon an ester with an alcohol soas to form another ester and another alcohol and removing bydistillation during the reaction a quantity of the alcohol formed so asto remove a constant boiling mixture of the alcohol and the ester added.

2. The process which comprises reacting upon an ester of an aliphaticacid and alcohol with an alcohol so as to form another ester and anotheralcohol, and removing by distillation during the reaction a quantityofthe alcohol formed so as to remove a constant boiling mixture of thealcohol and the ester added.

3. The process which comprises reacting upon methyl acetate with anotheralcohol so as to form another acetate and methyl alcohol, and removing aquantity of the methyl alcohol formed by distillation so as to remove aconstant boiling mixture of the methyl alcohol and the methyl acetateadded.

4. The process which comprises reacting upon an ester with an alcohol soas to form another ester and another alcohol, the process being carriedout continuously b the continuous addition of the ester and t e alouslycarrying the reaction beyond the point of equilibrium.

6. The process which comprises reacting upon an ester with an alcohol soas to form another ester and another alcohol and removing a quantity ofthe alcohol formed, the process being carried out continuously by thecontinuous addition of the ester and the alcohol added and continuouslycarrying the reactipn beyond the point of equilibrium.

7. The process which comprises reacting upon an ester with an alcohol soas to form another ester and another alcohol and removing a quantity ofthe alcohol formed by distillation, the process being carried outcontinuously by the continuous addition of the ester and the alcoholadded and continuously carrying the reaction beyond the point ofequilibrium. 8. The process which comprises reacting upon an ester withan alcohol so as to form another ester and another alcohol and removinga quantity of the alcohol formed by distillation so as to remove aconstant boiling mixture of the alcohol and the ester added, the processbeing carried out continuously by the continuous addition of the esterand the alcohol added and continuously carrying the reaction beyond thepoint of equilibrium.

9. The process which comprises reacting upon methyl acetate with anotheralcohol so as to form another acetate and methyl alcohol and removing aquantity alcohol formed by distillation so as to remove a constantboiling mixture of the methyl alcohol and the methyl acetate added, theprocess being carried out continuously by the continuous addition of theester and the alcohol added, and continuously carrying the reactionbeyond the point of equilibrium.

10. The process which comprises introducing amy alcohol and sulphuricacid into the top of a column still, introducing methyl acetate in thebottom thereof, allowing the amyl acetate and other products to flowinto a second still, heating the latter, and distilling oil the methylalcohol which is formed in the column still during the reaction.

In testimony that I claim the foregoing, I have hereunto set my handthis 26th day of January, 1921.

LLOYD M. BURGHART.

of the methyl-

